As I was approaching my 60th birthday, I vowed I would finally go to Ulta and get make up that was geared towards my skin tones. I never really wore anything other than blush, lipstick, and mascara as they are rather generic.

Having been a crossdresser since I was five (my mother told me that my neighbor friend and I used to sit on the front porch and put on my sisters’ old clothes), I got to the point where I wanted to be able to go out in public. I wanted to be able to comfortably go shopping and try on all of the clothes I wanted. Just being able to go into the lingerie section dressed as a woman allows me to feel comfortable touching the delicate items, to pick them up and imagine what they might feel like on instead of the feeling of being a bit of a perv in drab.

I got my courage up one Saturday, and in “Drab mode” I entered Ulta and looked for someone that appeared non-confrontational and open to helping me select the proper makeup for my skin tones. I chose a middle-aged woman, who seemed nice, and told her what I wanted: Foundation, Powder, Mascara, Eye Liner, Blush, Lip Stick and Lip Liner.

She seemed rather shocked and nervous, even more nervous than me, but she got all of the items together except for the eyeliner. She approached an adorable young woman at the Clinique counter, Stephanie, and asked if she could help me with eyeliner.

Stephanie asked me who the eyeliner is for, your wife or daughter. I bravely said, “It’s for me”. Much to my surprise and amazement, she responded with, “I think that’s great,” and high-fived me.

It was truly one of the most magical moments of my life; (I’m not exaggerating). I have always been ashamed and embarrassed about my odd little hobby. For the first time in my life, I felt a huge burden taken off my shoulders. I felt ecstatic and fell in love with Stephanie at that moment.

After I bought all of my makeup at Ulta, I went back the following week and talked to Stephanie (the Clinique Counter Manager) in Drab. I told her that I was wondering if she would give me a makeover, and she said she would love to, so I made an appointment for the following Saturday.

That day, I rented a hotel room near my house and brought over all of my girl clothes and got dressed up as best I could in my favorite LBD. I was scared to death to walk out of the Hotel and even more scared to walk into Ulta, but I did it. It was one of the highlights of my life. I’ve gone back to Ulta dozens of times to have makeovers from Stephanie, who is now one of my best friends and confidant.

Sitting on Stephanie’s stool, in the center of the store, was exhilarating and nerve wracking. I felt hypnotized as she applied foundation, powder, blush, lip liner, lipstick, and eye shadow. I was sitting in the middle of the store near the entrance and surrounded by other customers. I was aware of other salespeople watching me curiously, but I didn’t care. The attention Stephanie was giving to me was more important than my feelings of nervousness and unease at the situation.

Stephanie spent more than 45 minutes giving me my makeover. I felt so confident in my appearance that, for first time in my life, I went shopping en femme. I shopped every store in that strip mall that day and tried on all of the clothes I wanted, never once getting any odd little stares. One man even held the door to Black & White open for me. I did give Stephanie a card with a nice note and a big tip. They don’t promote tipping at Ulta (but everyone there appreciates it), and as long as you buy product the makeovers are free.

When I was finished shopping, I went back to the hotel and took this picture of myself. I used to love this dress.

 

 

 

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JackieBoy

Heterosexual Cross Dresser

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Emma
Lady
Member

Your smile lights up the room! I’m so happy for you. your so beautiful, and your confidence is glowing. I wish you the best and thank you for your story you go girl.

James North
Guest
James North

Hi you look great x

Lynda Jones
Duchess
Member

Jackie, what an awesome experience you look great , I have only had one makeover and it was awesome.

Nicole M
Duchess
Member

Hi Jackie, thats a lovely story and im Happy for you. Looking great there too. Ive never had someone else do my makeup… i would love it but not yet been out as Nicole.
And yes, i know that feeling when you have to take everthing off. I just enjoy dressing so much and keep that in my mind for the next time to get over the dressdown blues. X

Ambermaria Martinez
Duchess
Member

Omg nicole gurl what are you waiting for come out its WONDERFUL world out hear .I’ve been out for a long long time and feel so so MUCH HAPPIER in LIFE as anbermaria have WOMEN FRIENDS from work who know I dress and we have girl days out shopping and she helps me with my makeup and all my GOURGOUS clothes the way MOTHER used to when we had MOTHER and daughter days out

Holly Dolly
Lady
Member

WOW you look stunning – so much younger and so beautiful

Ambermaria Martinez
Duchess
Member

Omg what a BEAUTIFUL story how lucky are you that’s what I want and need to do also to have my makeup done buy a woman makeup artist. Who can help me with my own makeup. I’ve been a girl my entire LIFE since I’m 12 years old. I’m an only child with a BEAUTIFUL MOTHER who knows I’m HAPPIER as Ambermaria. Who ALWAYS knew I was dressing in her clothes all my teen years and FINALLY when I turned 18 yrs old she FINALLY met her DAUGHTER she ALWAYS knew I was. She just stood there and gave me… Read more »

Leah
Lady
Member

great story with a positive note to it. Glad you were able to find a supportive and accepting lady to assist you with your make over but even a step beyond and become a friend and confidant. I have yet to get a makeover, but it is on my bucket list!

Ambermaria Martinez
Duchess
Member

Hi leah sorry for late reply had tech issues. On having a woman do my makeup would make me feel more completely FEMININE. I ALWAYS watched and love how mother did her makeup. She did do mine before she moved away. That was when I was about 17.years old

Samantha Smith
Lady

Wow,beautiful!

Tammy CD
Duchess
Active Member

That was such a wonderful story. I really enjoyed hearing that story. I am extremely happy for you. That is really wonderful that your story nice. I am also glad for you that you got a great friend out of the deal. You look amazing my dear. Keep up the great work. I am proud of you.. Kisses

Samantha Z
Guest
Samantha Z

Super HOT you ROCK!!!

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